A quaint white building with a dark shingled roof, a flag, and a sign reading "Toys Ahoy".

Essex Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Essex holiday rentals

A cabin with a large window, surrounded by trees.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (182 reviews)
"Great property for quiet and a nice getaway. Great little places to eat and shop in the surrounding towns."
United States
Frank
The price is HK$993
HK$1,863 total
includes taxes & fees
1 Sept - 2 Sept
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A bedroom with a wooden bed, bedside lamps, a sofa, and a TV stand.

2. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (53 reviews)
"We enjoyed our stay"
United States
JM B.
The price is HK$924
HK$1,799 total
includes taxes & fees
8 Sept - 9 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
A large, white, multi-story building with a prominent tower and a flag on top.

3. Walk To Goodspeed Opera House!

Walk To Goodspeed Opera House!
East Haddam
9.4 out of 10, Exceptional, (40 reviews)
"Simple process, plenty of room, ample parking and no issues with noise from the business above. "
United States
Amber J.
The price is HK$1,144
HK$1,986 total
includes taxes & fees
15 Sept - 16 Sept
Walk To Goodspeed Opera House!
A cabin by a lake with a wooden exterior, a deck, and a small outdoor seating area.

4. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is HK$1,121
HK$2,323 total
includes taxes & fees
22 Sept - 23 Sept
Cozy Lakefront Tiny House
A living room with a grey sofa, an orange armchair, a small round table, and a glass-top coffee table.

5. The Tiny Cottage & Mini Farm

The Tiny Cottage & Mini Farm
Oakdale,
10.0 out of 10, Exceptional, (10 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is HK$952
HK$1,252 total
includes taxes & fees
2 Sept - 3 Sept
The Tiny Cottage & Mini Farm
A cozy room with a bed, a dining table set with bowls and spoons, and a view of a lake and trees.

6. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (9 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is HK$1,043
HK$2,226 total
includes taxes & fees
22 Sept - 23 Sept
Lakefront Boho Tiny House
A kitchen with a microwave, stove, and granite countertop. There is a dining area with a sofa and a coffee table.

7. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is HK$1,411
HK$2,581 total
includes taxes & fees
1 Sept - 2 Sept
The gardners Cottage 1 mile from long Island Sound - pet friendly
A stone pier leading to a beach with houses in the background.

8. Insta-worthy Couples Retreat: Perfect for romantic getaway!

Insta-worthy Couples Retreat: Perfect for romantic getaway!
Old Lyme
9.4 out of 10, Exceptional, (60 reviews)
"A beautiful little beach cottage that was just what the doctor ordered. A great place to unwind and take in the sea air."
United States
Emily M.
The price is HK$1,035
HK$2,341 total
includes taxes & fees
15 Sept - 16 Sept
Insta-worthy Couples Retreat: Perfect for romantic getaway!
A rocky shoreline with a beach and ocean in the background.

9. The Stern at Soundview · Beach+Ocean+Sunrise

The Stern at Soundview · Beach+Ocean+Sunrise
Old Lyme
9.0 out of 10, Wonderful, (4 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is HK$1,293
HK$2,432 total
includes taxes & fees
22 Sept - 23 Sept
The Stern at Soundview · Beach+Ocean+Sunrise
A rocky shoreline with a clear view of the ocean and a distant shoreline with buildings.

10. Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"Very peaceful community. Great accommodations!"
United States
Joseph O.
The price is HK$1,364
HK$2,520 total
includes taxes & fees
7 Sept - 8 Sept
Keel at Soundview · Beach+OceanView+Sunrise
A beach with waves, a clear sky, and a sandy shore.

11. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is HK$1,263
HK$2,947 total
includes taxes & fees
22 Sept - 23 Sept
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
A covered outdoor area with a stone patio, a grill, and Adirondack chairs overlooking a forested landscape.

12. Cozy Studio: Indoor Hot Tub & Inground Pool Access

Cozy Studio: Indoor Hot Tub & Inground Pool Access
3.0 star property
Montville
10.0 out of 10, Exceptional, (1 review)
"Everything from the price,location,tranquility, and the host Allen was awesome. We would go back in a heartbeat. Montville is beautiful."
United States
Eduardo
The price is HK$1,489
HK$3,367 total
includes taxes & fees
15 Sept - 16 Sept
Cozy Studio: Indoor Hot Tub & Inground Pool Access
A spacious, well-lit room with a high ceiling, large windows, and a cozy seating area with a sofa and chairs.

13. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is HK$2,508
HK$4,762 total
includes taxes & fees
21 Sept - 22 Sept
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

14. The Bay Cottage · Rocky Neck Park, Beach & Niantic

The Bay Cottage · Rocky Neck Park, Beach & Niantic
East Lyme
9.0 out of 10, Wonderful, (7 reviews)
"This house suited our needs for a place to stay while attending a nearby family reunion. Communication and check in were great and the house is very comfortable (very nice mattresses, sheets, pillows)."
United States
Sarah G.
The price is HK$1,374
HK$3,429 total
includes taxes & fees
15 Sept - 16 Sept
The Bay Cottage · Rocky Neck Park, Beach & Niantic
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

15. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (36 reviews)
"My son and I were here for two nights and had an excellent time. It was exactly as described and such a tastefully decorated and maintained place to stay. Would definitely stay here again if in the area!"
United States
Kate F.
The price is HK$980
HK$2,022 total
includes taxes & fees
7 Sept - 8 Sept
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A beach with a house in the background, a clear sky, and a calm sea.

16. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
10.0 out of 10, Exceptional, (1 review)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is HK$1,235
HK$2,868 total
includes taxes & fees
3 Sept - 4 Sept
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
A spacious living area with a wooden floor, a sofa set, a coffee table, and a fireplace.

17. Rogers Lake House (87) · CT College+Beach+USCGA

Rogers Lake House (87) · CT College+Beach+USCGA
Old Lyme
10.0 out of 10, Exceptional, (10 reviews)
"Very clean , spacious, and comfortable accomodations! Lovely location with lake across the street and short driving distance to local historical towns and the ocean."
United States
Cheryl H.
The price is HK$5,021
HK$8,744 total
includes taxes & fees
26 Sept - 27 Sept
Rogers Lake House (87) · CT College+Beach+USCGA
A large house with a pond and a fountain, surrounded by lush greenery.

18. ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO

ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
Norwich
9.8 out of 10, Exceptional, (18 reviews)
"Nice comfy stay in the beautiful room , Amanda was spot on with everything and very alert with any messages "
United States
Lenny R.
The price is HK$1,001
HK$2,624 total
includes taxes & fees
8 Sept - 9 Sept
ROMANTIC SPA RETREAT MINUTES TO MOHEGAN SUN CASINO
An aerial view of a marina with boats docked, surrounded by residential buildings and greenery.

19. Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (51 reviews)
"Great spot easy walk to the water and very close to town!"
United States
Genevieve G.
The price is HK$3,358
HK$5,865 total
includes taxes & fees
24 Sept - 25 Sept
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
A modern kitchen with white cabinets, a stainless steel refrigerator, a dishwasher, and a granite countertop.

20. Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (2 reviews)
"The home was very clean and welcoming."
United States
Michelle M.
The price is HK$1,724
HK$3,645 total
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Essex Hotel Reviews

The Spa at Norwich Inn

The Spa at Norwich Inn

10/10 Excellent
"Staff was very friendly and helpful at check in. They answered all my questions and told me everything that was included with my stay. The lobby and hotel in general was very well maintained. It was my first stay and I’ll definitely be back."
Michelle 1-night trip
Posted less than an hour ago
The Spa at Norwich Inn

Find out more about Essex

Search for holiday rentals in Essex on Expedia! You can easily find your home rentals, villas, holiday apartments in Essex using one of the methods below:

  • View our selection of featured holiday rentals in Essex
  • Use the map to find apartments and other holiday homes in the Essex neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Essex while they last

Look no further and take a look at our great range of rental properties in Essex!

Frequently asked questions

Are there holiday rentals in Essex?

Yes, there are holiday rentals in Essex close to Essex Steam Train, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Essex has a good selection of bars. Make sure you have time to check out the waterfront while you're in the area.

What are some of the best holiday rentals that Essex has to offer?

Waterfront Escape- 3BR Coastal Cottage w/ Boat Launch & Near Niantic Main Street: This holiday home rental outside of Essex is located on the waterfront, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Essex?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your Essex stay.

What’s there to see and do in Essex?

Essex Steam Train and Sweet Martha's are a couple of the family-friendly sights, whereas cultural attractions include Connecticut River Museum and Mashantucket Pequot Museum & Research Center. Connecticut River and Essex Island Marina are other places to visit while you're in town.

What’s a holiday rental in Essex like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Essex. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.